Diethylene Glycol → Tetrahydropyranyldiethyleneglycol

HRID 2276825노트

반응식

HRID 2276825 반응식
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][OH:6]

참가 물질

5

반응물 3

HCID 8117Diethylene GlycolHCID 8894TetrahydropyranHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 558984Tetrahydropyranyldiethyleneglycol수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 800 mL of CH2Cl2 were added diethylene glycol (57 mL, 0.6 mol) and p-toluenesulfonic acid monohydrate (5.7 g, 30 mmol) successively. Then tetrahydropyran (27.4 mL, 0.3 mol) was added dropwise at 0° C. The reaction mixture was stirred overnight and quenched with H2O, extracted with CH2Cl2, washed with H2O and brine successively, concentrated through rotary evaporation, and subjected to silica gel chromatography using CH2Cl2/MeOH as the eluent to afford compound 28 (32.5 g, 0.17 mol, 57% yield) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 4.59 (t, J=4.0 Hz, 1H), 3.85-3.80 (m, 2H), 3.68-3.64 (m, 4H), 3.59-3.55 (m, 3H), 3.48-3.44 (m, 1H), 2.98 (br, 1H), 1.81-1.76 (m, 1H), 1.71-1.65 (m, 1H), 1.59-1.46 (m, 4H).

후처리

  1. customquenched with H2O
  2. extractionextracted with CH2Cl2
  3. washwashed with H2O and brine successively
  4. concentrationconcentrated through rotary evaporation

출처 및 근거

ORD 기록
ord-7222c64e82ab460cade0a3f4f65a016c
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133114B2

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